Bromine → 4-Amino-3-bromo-5-nitropyridine

HRID 334479

반응식

HRID 334479 반응식
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[NH2:10])([O-:3])=[O:2].CC([O-])=O.[Na+].[Br:16]Br.C([O-])(O)=O.[Na+]>O.C(O)(=O)C>[Br:16][C:8]1[CH:7]=[N:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[C:9]=1[NH2:10]

참가 물질

7

반응물 4

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 5488034-Amino-3-nitropyridine

생성물 1

HCID 49975884-Amino-3-bromo-5-nitropyridine수율 87.4%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

A mixture of 3-nitropyridin-4-amine (LXVIII) (10 g, 71.88 mmol) and acetic acid (100 ml) was added to a sealed tube followed by addition of NaOAc (29.50 g, 359 mmol) and dropwise addition of bromine (4.43 ml 86.3 mmol) under stirring. The sealed tube was heated at 100° C. for overnight. The reaction mixture was concentrated under vacuum to obtain a solid which was dissolved in water, basified with saturated aqueous NaHCO3 and extracted with DCM. The combined organic extracts were dried and concentrated to produce 3-bromo-5-nitropyridin-4-amine (LXIX) as a yellow solid (13.7 g, 62.8 mmol, 87% yield). 1H NMR (DMSO-d6, 500 MHz) δ ppm 8.58 (s, 1H), 9.19 (s, 1H); ESIMS found for C5H4BrN3O2 m/z 218.1 (M+H).

후처리

  1. additionwas added to a sealed tube
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. customto obtain a solid which
  4. extractionextracted with DCM
  5. customThe combined organic extracts were dried
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-56d2a85b4fea4fb7a083f01211d03b09
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883822B2

연결된 노트

불러오는 중…